Metal-catalyzed Carbonylation Reactions : No Need for Carbon Monoxide. Literature Seminar Benjamin Ovadia
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1 Metal-catalyzed Carbonylation Reactions : No Need for Carbon Monoxide Literature Seminar Benjamin Ovadia 1
2 M-Catalyzed Carbonylative Coupling Pioneering work by Heck in the 70s Pd-Catalyzed alkoxycarbonylation Pd-Catalyzed amidocarbonylation Pd-Catalyzed formylation For review on Pd-ctalyzed carbonylative coupling: A. Brennführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2009, 48, X. F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011, 40, X. F. Wu, H. Neumann, M. Beller, Chem. Rev. 2013, 113, Q. Liu, H. Zhang, A. Lei, Angew. Chem. Int. Ed. 2011, 50,
3 M-Catalyzed Carbonylative Coupling CO is the most important C1 building block to introduce a carbonyle moiety Provide a straightforward access to valuable intermediates X CO is a Highly toxic gas X Carbonylation require high pressures of CO X Extreme caution to handle, store and transport For review on Pd-ctalyzed carbonylative coupling: A. Brennführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2009, 48, X. F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011, 40, X. F. Wu, H. Neumann, M. Beller, Chem. Rev. 2013, 113, Q. Liu, H. Zhang, A. Lei, Angew. Chem. Int. Ed. 2011, 50,
4 In-situ generation of CO from aldehydes - Rh-catalyzed Pauson-Khand type reaction (Kakiuchi and Shibata, 2002) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806 Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4,
5 In-situ generation of CO from aldehydes - Rh-catalyzed Pauson-Khand type reaction (Kakiuchi and Shibata, 2002) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806 Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4,
6 In-situ generation of CO from formamides - Pd-catalyzed aminocarbonylation of aryl bromides (Alterman, 2002) Wan, Y.; Alterman, M.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67,
7 In-situ generation of CO from formamides - Pd-catalyzed aminocarbonylation of aryl bromides (Alterman, 2002) Wan, Y.; Alterman, M.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67,
8 In-situ generation of CO from metal carbonyles - Pd-catalyzed aminocarbonylation of aryl iodide under MW irradiation (Larhed, 2003) Wannberg, J.; Larhed, M. J. Org. Chem. 2003, 68,
9 In-situ generation of CO from metal carbonyles Wu, X., Ekegren, J. K., Larhed, M. Organometallics 2006, 25, 1434 Odell, L. r.; Savmarker, J.; Larhed, M. Tetrahedron Lett. 2008, 49, 6115 Wieckowska, A.; Fransson, R.; Odell, L. R., Larhed, M. J. Org. Chem. 2011, 76, 978 9
10 In-situ generation of CO from chloroform -Pd-catalyzed hydroxycarbonylation of aryl iodide (Alper, 1993; Hull, 2015) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 3846 Gockel, S. N.; Hull, K. L. Org. Lett. 2015, 17,
11 In-situ generation of CO from chloroform -Pd-catalyzed hydroxycarbonylation of aryl iodide (Alper, 1993; Hull, 2015) Proposed mechanism for generation of CO Grushin, V. V.; Alper, H. Organometallics 1993, 12, 3846 Gockel, S. N.; Hull, K. L. Org. Lett. 2015, 17,
12 In-situ generation of CO from arylformate -Pd-catalyzed alcoxycarbonylation of aryl halide with phenylformate (Manabe, 2012) -Pd-catalyzed alcoxycarbonylation of aryl halide with arylformate (Tsuji, 2012) T. Ueda, H. Konishi, K. Manabe, Org. Lett. 2012, 14, T. Fujihara, T. Hosoki, Y. Katafuchi, T. Iwai, J. Terao, Y. Tsuji, Chem. Commun. 2012, 48,
13 In-situ generation of CO from arylformate -Pd-catalyzed carbonylation of aryl sulfonyl with arylformate (Beller, 2014) Li, H.; Neumann, H.; Beller, M.; Wu, X.-F. Ang. Chem. Int. Ed. 2014, 53, 1 13
14 In-situ generation of CO from arylformate -Pd-catalyzed carbonylation of aryl sulfonyl with arylformate (Beller, 2014) Li, H.; Neumann, H.; Beller, M.; Wu, X.-F. Ang. Chem. Int. Ed. 2014, 53, 1 14
15 In-situ generation of CO from arylformate -Pd-catalyzed carbonylation of aryl sulfonyl with arylformate (Beller, 2014) Li, H.; Neumann, H.; Beller, M.; Wu, X.-F. Ang. Chem. Int. Ed. 2014, 53, 1 15
16 Ex-situ generation of CO : Two-chamber reactors and CO precursors Friis, S.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594 P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133,
17 Ex-situ generation of CO : Two-chamber reactors and CO precursors - First generation precursor : pivaloyl chloride Commercially available Low cost Atom economy X Pollution of CO consuming chamber with isobutene gas Friis, S.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594 P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133,
18 Ex-situ generation of CO : Two-chamber reactors and CO precursors - Second generation precursors : Cogen and SilaCogen Friis, S.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594 P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133,
19 Ex-situ generation of CO : Two-chamber reactors and CO precursors - Application : Pd-catalyzed aminocarbonylation of aryl halide using COgen Friis, S.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594 P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133,
20 Ex-situ generation of CO : Two-chamber reactors and CO precursors - Application : Pd-catalyzed aminocarbonylation of aryl halide using COgen Friis, S.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594 P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133,
21 Ex-situ generation of CO : Two-chamber reactors and CO precursors - Application : Pd-catalyzed carbonylation of aryl halide using SilaCOgen Friis, S.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594 Friis, S.; Taaning, R. H., Lindhardt, A. T.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133,
22 Ex-situ generation of CO : Two-chamber reactors and CO precursors - Application : Pd-catalyzed carbonylation of aryl halide using SilaCOgen Friis, S.; Lindhardt, A. T.; Skrydstrup, T. Acc. Chem. Res. 2016, 49, 594 Friis, S.; Taaning, R. H., Lindhardt, A. T.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133,
23 Carbonylation Reactions Using CO 2 as CO-Surrogate Liu, Q.; Wu, L.; Fleisher, I.; Jackstell, R.; Beller, M. Nat. Commun. 2014, 6, 5933 Morimoto, T.; Kakiuchi, K. Angew. Chem. Int. ed. 2004, 43,
24 Carbonylation Reactions Using CO 2 as CO-Surrogate Catalytic production of CO from reduction of CO 2 - Using H 2 as reductant Tominaga, K.-I.; Sasaki, Y. Cat. Commun. 2000, 1, 1 Liu, Q.; Wu, L.; Fleisher, I.; Selent, D.; Franke, R.; Jackstell, R.; Beller, M. Chem. Eur. J. 2014, 20, 6888 Ostapowiz, T. G.; Schmitz, M.; Krystof, M.; Klankermayer, J.; Leitner, W. Angew. Chem. Int. ed. 2013, 52,
25 Carbonylation Reactions Using CO 2 as CO-Surrogate Catalytic production of CO from reduction of CO 2 - Using H 2 as reductant Tominaga, K.-I.; Sasaki, Y. Cat. Commun. 2000, 1, 1 Liu, Q.; Wu, L.; Fleisher, I.; Selent, D.; Franke, R.; Jackstell, R.; Beller, M. Chem. Eur. J. 2014, 20, 6888 Ostapowiz, T. G.; Schmitz, M.; Krystof, M.; Klankermayer, J.; Leitner, W. Angew. Chem. Int. ed. 2013, 52,
26 Carbonylation Reactions Using CO 2 as CO-Surrogate Catalytic production of CO from reduction of CO 2 - Using Alcohol as reductant Wu, L.; Liu, Q.; Fleisher, I.; Jackstell, R.; Beller, M. Nat. Commun. 2013, 5, 1 26
27 Carbonylation Reactions Using CO 2 as CO-Surrogate Catalytic production of CO from reduction of CO 2 - Copper catalyzed oxygen abstraction of diboron or Borosilane Laitar, D. S.; Muller, P., Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, Kleeberg, C.; Cheung, M. S.; Lin, Z.; Marder, T. B. J. Am. Chem. Soc. 2011, 133,
28 Fluoride-Catalyzed Conversion of CO 2 to CO Using Disilanes Lescot, C.; Nielsen, D. U.; Makarov, I. S.; Lindhart, A. T.; Daasbjerg, K., Skrydstrup, T. J. Am. Chem. Soc. 2014, 136,
29 Fluoride-Catalyzed Conversion of CO 2 to CO Using Disilanes Catalytic production of CO from reduction of CO 2 - Proposed pathway Stoechiometric silicon by-product Lescot, C.; Nielsen, D. U.; Makarov, I. S.; Lindhart, A. T.; Daasbjerg, K., Skrydstrup, T. J. Am. Chem. Soc. 2014, 136,
30 Fluoride-Catalyzed Conversion of CO 2 to CO Using Disilanes Hiyama-Denmark cross-coupling Cooperative redox activation of CO 2 /Carbonylative Hiyama-Denmark coupling Lian, Z.; Nielsen, D. U.; Lindhart, A. T.; Daasbjerg, K., Skrydstrup, T. Nat. Commun. 2016, 7,
31 Fluoride-Catalyzed Conversion of CO 2 to CO Using Disilanes Cooperative redox activation of CO 2 /Carbonylative Hiyama-Denmark coupling Lian, Z.; Nielsen, D. U.; Lindhart, A. T.; Daasbjerg, K., Skrydstrup, T. Nat. Commun. 2016, 7,
32 Fluoride-Catalyzed Conversion of CO 2 to CO Using Disilanes Cooperative redox activation of CO 2 /Carbonylative Hiyama-Denmark coupling Lian, Z.; Nielsen, D. U.; Lindhart, A. T.; Daasbjerg, K., Skrydstrup, T. Nat. Commun. 2016, 7,
33 Conclusion Ex-situ generation of CO using CO precursor in a double chamber Cooperative redox activation of CO 2 /Carbonylative Hiyama-Denmark coupling 33
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